Synthesis 2004(9): 1527-1531  
DOI: 10.1055/s-2004-822393
PAPER
© Georg Thieme Verlag Stuttgart · New York

Copper-Mediated Simple and Efficient Synthesis of Tribenzohexadehydro[12]annulene and Its Derivatives

Masahiko Iyoda*, Siriwan Sirinintasak, Yoshihiro Nishiyama, Anusorn Vorasingha, Fatema Sultana, Kazumi Nakao, Yoshiyuki Kuwatani, Haruo Matsuyama, Masato Yoshida, Yoshihiro Miyake
Department of Chemistry, Graduate School of Science, Tokyo Metropolitan University, Hachioji, Tokyo 192-0397, Japan
Fax: +81(426)772525; e-Mail: iyoda-masahiko@c.metro-u.ac.jp;
Further Information

Publication History

Received 4 May 2004
Publication Date:
26 May 2004 (online)

Abstract

A simple and efficient synthesis of tribenzohexadehydro[12]annulene and its derivatives was carried out using coupling reaction of acetylenes with iodoarenes in the presence of catalytic amounts of CuI and PPh3, together with three equivalents of K2CO3 in DMF. This synthetic procedure was applied to the synthesis of a large annulenoannulene derivative.

18

The silver complex (2c)2 AgBF4: 1H NMR (CD2Cl2): δ = 0.87 (m, 24 H), 1.02 (m, 16 H), 1.48 (m, 16 H), 2.39 (m, 8 H), 2.54 (m, 8 H), 7.09 (s, 4 H), 7.14 (s, 4 H), 7.69 (s, 2 H); LDTOF-MS: m/z calcd for C148H164Ag: 2048.19; found: 2049.5.